John 16:23

“In that day ye shall ask me nothing, etc.] Meaning, not the whole Gospel dispensation, so often called, in prophetic language, “that day”; and is, in the New Testament, opposed to the night of Jewish and Gentile darkness; and, in comparison of the former dispensation, is a time of great spiritual light and knowledge: nor the latter part of that day, when there will be no night of darkness and desertion, of error and security, of affliction and persecution, with the church; when the earth shall be filled with the knowledge of the Lord; when all the children of God shall be taught of him, and there will be no need to say, know the Lord, for all shall know him, from the least to the greatest:…”

“In that day--of the dispensation of the Spirit (as in Joh 14:20). ye shall ask--inquire of me nothing--by reason of the fulness of the Spirit's teaching (Joh 14:26; Joh 16:13; and compare Jo1 2:27).”

“In that day - After my resurrection and ascension. Ye shall ask me nothing - The word rendered “ask” here may have two significations, one to ask by way of inquiry, the other to ask for assistance. Perhaps there is reference here to both these senses. While he was with them they had been accustomed to depend on him for the supply of their wants, and in a great degree to propose their trials to him, expecting his aid. See Matthew 8:25; John 11:3. They were also dependent on his personal instructions to explain to them the mysteries of his religion, and to remove their perplexities on the subject of his doctrines. They had not sought to God through him as the Mediator, but they had directly…”

“Ye shall not question me about any thing - Which you do not now understand. You will not need to inquire of me; for you will know all things clearly. Whatsoever ye shall ask - Knowledge, love, or any thing else, he will give it - Our Lord here gives us a charte blanche. Believer, write down what thou wilt. He had said, Joh 14:13, I will do it, where the discourse was of glorifying the Father through the Son. Here, speaking of the love of the Father to believers, he saith, He will give it. John 16:24”

“16:23-24 Ask . . . and you will receive: Two notable effects of the resurrection are the joy of understanding and the joy of successful prayer. The disciples would no longer experience the confusion described in 16:16-18.”

“ask: Joh 16:19, Joh 13:36, Joh 13:37, Joh 14:5, Joh 14:22, Joh 15:15, Joh 21:20, Joh 21:21 Whatsoever: Joh 14:13, Joh 14:14, Joh 15:7, Joh 15:16; Isa 65:24; Mat 7:7, Mat 21:22; Eph 2:18, Eph 3:14-20; Ti1 2:5, Ti1 2:6; Heb 4:14-16, Heb 7:25, Heb 7:26, Heb 10:19-23; Jo1 2:1, Jo1 5:14-16 John 16:24”